CAS 71-63-6|Digitoksin|Tardigal|Digitoxinum|Digitalin|Crystodigin|Digitoxoside|digitoxin|Unidigin|Digitoxin|4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5...

General Information

Structure

Molecular Formula

C₄₁H₆₄O₁₃

Molecular Mass

764.93906

Exact Mass

764.43469211

Charge

InChI

InChI=1S/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1

InChIKey

WDJUZGPOPHTGOT-XUDUSOBPSA-N

Canonic Smiles

O=C1OCC(=C1)[C@H]1CC[C@]2([C@]1(C)CC[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@@H](C2)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O)O

Isomeric Smiles

O[C@@]12[C@H]3[C@@H]([C@@]4([C@H](CC3)C[C@@H](O[C@@H]3O[C@@H]([C@@H](O[C@@H]5O[C@@H]([C@@H](O[C@@H]6O[C@@H]([C@@H](O)[C@@H](O)C6)C)[C@@H](O)C5)C)[C@@H](O)C3)C)CC4)C)CC[C@@]1([C@H](CC2)C1=CC(=O)OC1)C

Calculated Properties

Provided by Enamine

CLogP

2.85

H Donor

Polar Surface Area

182.83

Rotatable Bonds

JChem

Polar Surface Area

182.83

H Donor

H Acceptors

Rotatable Bonds

Lipinski's Rule of Five

false

Log P

3.60

LogD (pH = 5.5)

3.60

LogD (pH = 7.4)

3.60

Acid pKa

13.03

Molar Refractivity

191.72

Polarizability

78.34

LOG S

-3.79

Data Source

Names and Identifiers

Synonyms

DigitoksinDigitoxinumDigitalinDigitoxosideDigitoxin5β,20(22)-Cardenolide-3β,14-diol-3-(O-2,6-dideoxy-β-D-ribo-hexopyranosyl-[1→4]-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-[1→4]-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy洋地黄毒苷Digitoxin

Brand Name

TardigalCrystodiginUnidiginDigitaline

IUPAC Traditional name

digitoxin

IUPAC name

4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]-2,5-dihydrofuran-2-one 4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-7-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2,5-dihydrofuran-2-one

API Name

Digitoxin

Names and Identifiers

Registration numbers

PubChem CID

441207

CAS Number

71-63-6

PubChem SID

4650603516096466924893976

EC Number

Beilstein Number

MDL Number

CHEMBL

Unique Ingredient Identifier

CHEBI ID

ATC CODE

DrugBank ID

Wikipedia Title

Chemspider ID

KEGG ID

Registration numbers

Properties

Physical Property

Solubility

0.0039 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

chloroform: soluble

Hydrophobicity(logP)

1.85 [SANGSTER (1993)]

Melting Point

256-257°C

240 °C (dec.)(lit.)

Apperance

powder

[α]23/D +5.4°, c = 1.2 in dioxane

[α]20/D +17±1°, 7 hr, c = 2% in chloroform

Safety Information

R:23/25-33

23/25-33

151

Pharmacology Properties

5~7 days

95% (Oral)

Liver

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB01396

Drug Groups

approved

Description

A cardiac glycoside sometimes used in place of digoxin. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665)

Indication

For the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure.

Pharmacology

Digitoxin is a cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting (From Martindale, The Extra Pharmacopoeia, 30th ed, p665). Unlike digoxin (which is eliminated from the body via the kidneys), it is eliminated via the liver, so could be used in patients with poor or erratic kidney function. However, it is now rarely used in current UK medical practice. While there have been several controlled trials which have shown digoxin to be effective in a proportion of patients treated for heart failure, there is not the same strong evidence base for digitoxin, although it is presumed to be similarly effective.

Toxicity

Digitoxin exhibits similar toxic effects to the more-commonly used digoxin, namely: anorexia, nausea, vomiting, diarrhoea, confusion, visual disturbances, and cardiac arrhythmias.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

References

• Belz GG, Breithaupt-Grogler K, Osowski U: Treatment of congestive heart failure--current status of use of digitoxin. Eur J Clin Invest. 2001;31 Suppl 2:10-7. [Pubmed]

• Kurowski V, Iven H, Djonlagic H: Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies. Intensive Care Med. 1992;18(7):439-42. [Pubmed]

• Johansson S, Lindholm P, Gullbo J, Larsson R, Bohlin L, Claeson P: Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. Anticancer Drugs. 2001 Jun;12(5):475-83. [Pubmed]

• Hippius M, Humaid B, Sicker T, Hoffmann A, Gottler M, Hasford J: Adverse drug reaction monitoring--digitoxin overdosage in the elderly. Int J Clin Pharmacol Ther. 2001 Aug;39(8):336-43. [Pubmed]

External Links

• [Wikipedia]

Crystalline

D5878

包装
1, 5, 10 g in glass bottle
250, 500 mg in glass bottle

Molecule Details

References

PubChem Literature

From Data Sources

• Belz GG, Breithaupt-Grogler K, Osowski U: Treatment of congestive heart failure--current status of use of digitoxin. Eur J Clin Invest. 2001;31 Suppl 2:10-7. Pubmed

• Kurowski V, Iven H, Djonlagic H: Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies. Intensive Care Med. 1992;18(7):439-42. Pubmed

• Hippius M, Humaid B, Sicker T, Hoffmann A, Gottler M, Hasford J: Adverse drug reaction monitoring--digitoxin overdosage in the elderly. Int J Clin Pharmacol Ther. 2001 Aug;39(8):336-43. Pubmed

• Johansson S, Lindholm P, Gullbo J, Larsson R, Bohlin L, Claeson P: Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. Anticancer Drugs. 2001 Jun;12(5):475-83. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

Brand Name

TardigalCrystodiginUnidiginDigitaline

IUPAC Traditional name

digitoxin

IUPAC name

API Name

Digitoxin

Registration numbers

PubChem CID

441207

CAS Number

71-63-6

PubChem SID

4650603516096466924893976

EC Number

Beilstein Number

MDL Number

CHEMBL

Unique Ingredient Identifier

CHEBI ID

ATC CODE

DrugBank ID

Wikipedia Title

Chemspider ID

KEGG ID

References

PubChem Literature

From Data Sources

• Belz GG, Breithaupt-Grogler K, Osowski U: Treatment of congestive heart failure--current status of use of digitoxin. Eur J Clin Invest. 2001;31 Suppl 2:10-7. Pubmed

• Kurowski V, Iven H, Djonlagic H: Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies. Intensive Care Med. 1992;18(7):439-42. Pubmed

• Hippius M, Humaid B, Sicker T, Hoffmann A, Gottler M, Hasford J: Adverse drug reaction monitoring--digitoxin overdosage in the elderly. Int J Clin Pharmacol Ther. 2001 Aug;39(8):336-43. Pubmed

• Johansson S, Lindholm P, Gullbo J, Larsson R, Bohlin L, Claeson P: Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. Anticancer Drugs. 2001 Jun;12(5):475-83. Pubmed

Bioactivity

PubChem BioAssay

Properties

Physical Property

Solubility

0.0039 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

chloroform: soluble

Hydrophobicity(logP)

1.85 [SANGSTER (1993)]

Melting Point

256-257°C

240 °C (dec.)(lit.)

Apperance

powder

[α]23/D +5.4°, c = 1.2 in dioxane

[α]20/D +17±1°, 7 hr, c = 2% in chloroform

Safety Information

R:23/25-33

23/25-33

151

Pharmacology Properties

5~7 days

95% (Oral)

Liver

Molecule Details

DrugBank

DB01396

Drug Groups

approved

Description

Indication

For the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure.

Pharmacology

Toxicity

Digitoxin exhibits similar toxic effects to the more-commonly used digoxin, namely: anorexia, nausea, vomiting, diarrhoea, confusion, visual disturbances, and cardiac arrhythmias.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

References

• Belz GG, Breithaupt-Grogler K, Osowski U: Treatment of congestive heart failure--current status of use of digitoxin. Eur J Clin Invest. 2001;31 Suppl 2:10-7. [Pubmed]

• Kurowski V, Iven H, Djonlagic H: Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies. Intensive Care Med. 1992;18(7):439-42. [Pubmed]

• Johansson S, Lindholm P, Gullbo J, Larsson R, Bohlin L, Claeson P: Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. Anticancer Drugs. 2001 Jun;12(5):475-83. [Pubmed]

• Hippius M, Humaid B, Sicker T, Hoffmann A, Gottler M, Hasford J: Adverse drug reaction monitoring--digitoxin overdosage in the elderly. Int J Clin Pharmacol Ther. 2001 Aug;39(8):336-43. [Pubmed]

External Links

• [Wikipedia]

Crystalline

D5878

包装
1, 5, 10 g in glass bottle
250, 500 mg in glass bottle

Molecule

ID:1207